Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
Intramolecular homolytic substitution at selenium: Synthesis of novel selenium-containing vitamin E analogues
Autore:
Al-Maharik, N; Engman, L; Malmstrom, J; Schiesser, CH;
Indirizzi:
Univ Uppsala, Inst Chem, Dept Organ Chem, S-75121 Uppsala, Sweden Univ Uppsala Uppsala Sweden S-75121 Organ Chem, S-75121 Uppsala, Sweden Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia Univ Melbourne Melbourne Vic Australia 3010 elbourne, Vic 3010, Australia
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 19, volume: 66, anno: 2001,
pagine: 6286 - 6290
SICI:
0022-3263(20010921)66:19<6286:IHSASS>2.0.ZU;2-F
Fonte:
ISI
Lingua:
ENG
Soggetto:
PENTOSE STARTING MATERIALS; THIOL PEROXIDASE-ACTIVITY; FREE-RADICAL SYNTHESIS; LIPID-PEROXIDATION; ORGANOTELLURIUM COMPOUNDS; ANTIOXIDANT ACTIVITY; DIARYL TELLURIDES; TERTIARY ALCOHOLS; CONTAINING HETEROCYCLES; S(RN)1/S(H)I REACTIONS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
42
Recensione:
Indirizzi per estratti:
Indirizzo: Engman, L Univ Uppsala, Inst Chem, Dept Organ Chem, Box 531, S-75121 Uppsala, Sweden Univ Uppsala Box 531 Uppsala Sweden S-75121 121 Uppsala, Sweden
Citazione:
N. Al-Maharik et al., "Intramolecular homolytic substitution at selenium: Synthesis of novel selenium-containing vitamin E analogues", J ORG CHEM, 66(19), 2001, pp. 6286-6290

Abstract

Treatment of 1-(benzylselenenyl)-5-butyl-5-nonanoI (10) with oxalyl chloride followed by the sodium salt of N-hydroxypyridine-2-thione afforded the corresponding pyridine-2-thione-N-oxycarbonyI (PTOC) oxalate ester which wasnot isolated but immediately heated to provide 2,2-dibutylselenane (7). This transformation presumably involves a tertiary alkyl radical that undergoes intramolecular homolytic substitution at selenium with loss of the benzyl radical to provide the selenium-containing ring system (7). A similar protocol, when applied to 1-(2-benzylselenenyl-5-methoxyphenyl)-3-methyl3-heptanol (18) and 1-(2-benzylselenenyl-5-methoxyphenyl)-3,7,11,15-tetramethyl-3-hexadecanoI (19), followed by deprotection, afforded the selenium-containing alpha -tocopherol analogues 4 and 1f, respectively, in moderate yields. To the best of our knowledge, these transformations represent the first examples of tertiary radicals involved in homolytic substitution chemistry at selenium.td2

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 27/11/20 alle ore 01:40:40